1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione
• CAS No.: 864237-69-4
• Molecular Formula: C₅₇H₅₂N₂O₉
• Molecular Weight: 909.048
• Mol file: 864237-69-4.mol

Synonyms:1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione

Chemical Property of 1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione

There total 1 articles about 1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 48.0%

(2R,3R,3aS,9aR)-3-Hydroxy-2,9a-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one + benzyl bromide (100-39-0) → 1-[3,4-anhydro-1,6-di-O-(4-monomethoxy)-trityl-β-D-psicofuranosyl]uracil + 1-{(2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione (864237-71-8) + (2R,3R,3aS,9aR)-3-Benzyloxy-2,9a-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one (864237-68-3) + 1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione (864237-69-4)

Guidance literature:

(2R,3R,3aS,9aR)-3-Hydroxy-2,9a-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one; With sodium hydride; In tetrahydrofuran; at 0 - 4 ℃; for 0.0833333h;

benzyl bromide; In tetrahydrofuran; at 4 - 20 ℃; for 20h;

DOI:10.1055/s-2005-871547

Reference yield: 87.0%

1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione (864237-69-4) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (2R,3S,4R,5R)-4-benzyloxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (864237-78-5)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 20h;

DOI:10.1055/s-2005-871547

Reference yield:

1-{(2R,3S,4S,5R)-4-Benzyloxy-3-hydroxy-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione (864237-69-4) → 1-((1R,3R,4R,5R)-4-Benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidine-2,4-dione (864237-73-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / pyridine / 20 h / 0 - 20 °C

2: 89 percent / p-TsOH / CHCl₃; methanol / 0.17 h / 20 °C

3: 46 percent / MeONa / methanol / 5 h / Heating

With pyridine; sodium methylate; toluene-4-sulfonic acid; In methanol; chloroform;

DOI:10.1055/s-2005-871547

upstream raw materials:

benzyl bromide

Downstream raw materials:

Methanesulfonic acid (2R,3S,4R,5R)-4-benzyloxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-bis-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester

1-((1R,3R,4R,5R)-4-Benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidine-2,4-dione

4-Amino-1-((1R,3R,4R,5R)-4-benzyloxy-3-hydroxymethyl-2,6-dioxa-bicyclo[3.2.0]hept-1-yl)-1H-pyrimidin-2-one

Acetic acid (1R,3R,4R,5R)-4-benzyloxy-1-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,6-dioxa-bicyclo[3.2.0]hept-3-ylmethyl ester